I’ve said it before, and I’ll keep saying it: the most important thing you can do with your writing is build trust.
Trust doesn’t come from sounding smart. It comes from making your reader feel like you care about them.
Today, we’re going to cover the most stupidly easy way to do this. And it has nothing to do with the words on the page—
It’s all about how you arrange them.
-Kristin 🍷
🍻 In today’s issue:
✏️ Sentence School: This is the best way to be kind to your reader.
🥃 The Writer’s Pour: Try reformatting your shit. Just see how it feels.
🤖 Robot Pals: AI is actually really good at formatting.
🎙️ Drunk Talk: Shitty Experiences = Great Content


Roman is definitely the nicest of the Roys. Source: Giphy
It won’t kill you to be kind to your reader
Thoughtful formatting has one function — kindness to your reader.
So what do I mean when I say “formatting”?
This applies to anything that impacts how your words are displayed.
For instance, you would never publish your blog in a yellow comic sans font on a lavender background. Because people would get dizzy trying to read that shit, right?
Well, there’s a good chance you’ve adopted some formatting habits that aren’t quite so terrible, but certainly don’t do your readers any favors.
For instance — as much as I love Paul Graham’s essays, I don’t think he’s thinking about how easy it is for his audience to read them. And when you have his level of magnetic success, having completely changed the consciousness of an entire industry, maybe you don’t need to.
But I would argue that you still should.
As someone who is trying to earn trust through business storytelling, kindness to your reader is hella important.
And it’s incredibly simple to master.
Here’s how to do it. 👇
Step 1 — Write in the format it’s going to be read
This can be done by simply narrowing the margins in the word processor you’re using to approximately 5 inches.
This will make those 3-4 line paragraphs 5-6 lines, and you’ll begin noticing walls of text that will make readers go cross-eyed if they’re reading your story on a mobile phone or in an email.

Adjust your margins before you write to avoid walls of text.
Generally speaking, if you’re not writing a book, you need much shorter paragraphs than you think, and you might find that many of your paragraphs are just a single sentence.
And as you learned a few weeks ago, rhythm is one of the most important style elements, so be sure to vary your sentence and paragraph length.
Your 8th grade grammar teacher isn’t breathing down your neck anymore. You don’t need five sentences in a single paragraph.
Step 2 — Break it up
If your story is more than a few hundred words, it should probably be broken up into sections with sub-headers. Think of those sub-headers as sub-hooks, enticing someone who might be skimming your article to read deeper.
Your subheader should be one of three things:
The first line of the first paragraph of that section. If it’s short and punchy, that’s a great way to do it.
A description of what happens in that section.
Or an emotional exclamation that describes the overall “mood” of that section
There’s no hard-and-fast rule about how many words each section should be — it should be broken up based on natural shifts in the story, such as a transition between acts, a flashback, or a shift in topic.
Some sections will be longer than others, and that’s ok.
Step 3 — Bullet, bold, and emoji where it feels right
Do you have a long paragraph where you’re listing things? Turn that into bullet points. Want to add extra context? Turn the bullet points into emojis that visually represent the theme of that point.
And don’t forget to bold important shit. If someone is skimming your essay, this will help them catch the most useful nuggets.
Remember:
🖼️ Pictures (even emojis) are stronger than words.
🧠 Bullets are easier on the brain than listed paragraphs.
🙏 And readers will thank you for directing them to what’s most important.


Dive into some exercises to put what you’ve just learned about thoughtful formatting into practice. 👇️
Exercise #1 - Short ⏱
Look through the last few things you’ve written, and identify at least one place where you could have created a bulleted list rather than listing things in paragraph form.
Play with using emojis and bullets. It may not always feel right, but you’ll begin to get a sense for when it’s most appropriate.
Here’s an example:
UNFORMATTED
As chaotic and miserable as all this was, we f*cking nailed it. We exceeded our revenue target by $200k, exceeded our profit target by $300k, earned an 82% NPS (the highest ever at Rockefeller Center), and we did it all safely, without a single case of Covid.
FORMATTED
As chaotic and miserable as all this was, we f*cking nailed it.
💰 We exceeded our revenue target by $200k.
📈 We exceeded our profit target by $300k.
🥇 We earned an 82% NPS, the highest ever at Rockefeller Center.
😷 And we did it all safely, without a single case of Covid.
Exercise #2 – Long ⏳
Grab something you’ve already written that is more than 400 words, and reformat it to include:
-Shorter paragraphs
-Subheaders
-At least one bulleted list
-Add emojis and bold, where appropriate
For examples, browse some back issues of Drunk Business Advice.
Exercise #3 – Reflective 🧠
Start paying attention to the formatting of the shit you read online.
What’s easy to read? What’s difficult?
How would you reformat the stuff that makes you go cross-eyed?


It really is. Source: Giphy
Of all the things you shouldn’t let AI do, reformatting your writing isn’t one of them
Personally, I like writing and formatting simultaneously. It helps me organize my thoughts.
But if you’re someone who would rather get the words on the page, and worry about formatting later, you’re in luck—
AI is pretty damn good at this.
Just give it your unformatted writing with this prompt:
I’m going to give you an essay that I would like you to format so that it’s easier to read. Do NOT change the words or content. Here is what I want you to do:
-Break up any long paragraphs that would extend longer than 5 lines on a mobile phone view.
-Add subheaders where appropriate. The subheaders should be one of three things: 1) The first line of the first paragraph of that section if it’s short, 2) A description of what happens in that section, or 3) An emotional exclamation that describes the overall “mood” of that section.
-Create bulleted lists out of any lists within paragraphs, where appropriate. Add emojis to those lists if it makes sense, or anywhere it may enhance the reader experience. And bold any important words, phrases, or lines.
Are you ready?
As always, remember that the AI may go a little overboard here. You probably won’t want to use all of the formatting suggestions, but this prompt will give you plenty of great options to choose from.
Use your good human sense.


Ahhh. Beautiful UN week in Midtown Manhattan. Image source: Al Jazeera
I’ve been surrounded by asshole world leaders all week
We just wrapped up what’s known as “Gridlock Week” here in NYC.
However, you might know it as the United Nations General Assembly. 193 heads of state and foreign ministers descended upon New York for the 80th General Assembly, and their mere presence in my neighborhood erupted in chaos at every turn.
🇮🇷 My block was shut down because the President of Iran was staying at the hotel across the street.
🇺🇸 I got trapped in President Trump’s motorcade on 5th Avenue, and missed a doctor’s appointment. (Apparently so did France’s President Macron, so I’m not alone in that one.)
🚨 And the sirens have been goddamn relentless.
Before I was a writer, the UN General Assembly was just a massive inconvenience that I dreaded every year.
But becoming a writer inspired one of the most positive mindset shifts I’ve ever had—
Shitty Experiences = Great Stories
These days, I view the world through the lens of storytelling. When bad things happen to me, I try to surface meaning from them, or at the very least, frame them as entertaining anecdotes.
This doesn’t just help me deepen my well of content — it actually makes me a happier person.
So the next time you’re stuck in a frustrating situation, just remember that your worst moments make the best stories.
I don’t take my place in your inbox for granted.
It’s an honor to be welcomed into your world, and I know I have to work to continue to earn it, week after week. So if you have feedback, or if there’s a topic you want me to cover, just hit reply and tell me!
And if you love Drunk Writing Advice, consider sharing it with a friend. 🥰